CA3049678A1 - Composes utiles pour le traitement de troubles du tractus digestif - Google Patents
Composes utiles pour le traitement de troubles du tractus digestif Download PDFInfo
- Publication number
- CA3049678A1 CA3049678A1 CA3049678A CA3049678A CA3049678A1 CA 3049678 A1 CA3049678 A1 CA 3049678A1 CA 3049678 A CA3049678 A CA 3049678A CA 3049678 A CA3049678 A CA 3049678A CA 3049678 A1 CA3049678 A1 CA 3049678A1
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- Prior art keywords
- inden
- ethoxy
- oxy
- dihydro
- chloro
- Prior art date
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 69
- 208000035475 disorder Diseases 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 54
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- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 28
- 208000020832 chronic kidney disease Diseases 0.000 claims abstract description 27
- 206010020772 Hypertension Diseases 0.000 claims abstract description 23
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 577
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 272
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 264
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 244
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 225
- -1 C4-C8cycloalkenyl Chemical group 0.000 claims description 199
- 239000004202 carbamide Substances 0.000 claims description 187
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 177
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 174
- 125000000623 heterocyclic group Chemical group 0.000 claims description 171
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 170
- 125000001072 heteroaryl group Chemical group 0.000 claims description 104
- 229910052757 nitrogen Inorganic materials 0.000 claims description 100
- 229910052736 halogen Inorganic materials 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 93
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- 150000002367 halogens Chemical group 0.000 claims description 66
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- 125000005647 linker group Chemical group 0.000 claims description 58
- 239000011734 sodium Substances 0.000 claims description 55
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- 125000005842 heteroatom Chemical group 0.000 claims description 51
- 230000002401 inhibitory effect Effects 0.000 claims description 50
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 48
- 229910052698 phosphorus Inorganic materials 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 229910052708 sodium Inorganic materials 0.000 claims description 37
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 36
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 33
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
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- 230000035699 permeability Effects 0.000 claims description 29
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- 241000124008 Mammalia Species 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
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- 230000001404 mediated effect Effects 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
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- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- WNWOGOMGWXFMIZ-WMZOPIPTSA-N (1S,2S)-4,6-dichloro-N,N-dimethyl-1-(2-methylphenoxy)-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=C(C=CC=C1)C)N(C)C WNWOGOMGWXFMIZ-WMZOPIPTSA-N 0.000 claims description 16
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- 125000003342 alkenyl group Chemical group 0.000 claims description 15
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- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 14
- YSERCIHBCXZJHY-HKUYNNGSSA-N (1S,2S)-6-chloro-2-(dimethylamino)-1-(2-methylphenoxy)-2,3-dihydro-1H-indene-4-carbonitrile Chemical compound ClC1=CC(=C2C[C@@H]([C@H](C2=C1)OC1=C(C=CC=C1)C)N(C)C)C#N YSERCIHBCXZJHY-HKUYNNGSSA-N 0.000 claims description 13
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 12
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 208000011580 syndromic disease Diseases 0.000 claims description 12
- 206010016654 Fibrosis Diseases 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 230000007882 cirrhosis Effects 0.000 claims description 11
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 9
- 208000030053 Opioid-Induced Constipation Diseases 0.000 claims description 9
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 9
- 208000019423 liver disease Diseases 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 8
- 208000038016 acute inflammation Diseases 0.000 claims description 8
- 230000006022 acute inflammation Effects 0.000 claims description 8
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- 206010047115 Vasculitis Diseases 0.000 claims description 7
- 206010047642 Vitiligo Diseases 0.000 claims description 7
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 claims description 7
- 208000004631 alopecia areata Diseases 0.000 claims description 7
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- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims description 7
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
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- ZGOFCJCZWCXORQ-WMZOPIPTSA-N (1S,2S)-4,6-dichloro-1-(2-fluoro-5-methylphenoxy)-N,N-dimethyl-2,3-dihydro-1H-inden-2-amine Chemical compound ClC1=C2C[C@@H]([C@H](C2=CC(=C1)Cl)OC1=CC(=CC=C1F)C)N(C)C ZGOFCJCZWCXORQ-WMZOPIPTSA-N 0.000 claims description 3
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Classifications
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- C—CHEMISTRY; METALLURGY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Abstract
La présente invention concerne des composés et des procédés pour le traitement de troubles associés à une rétention de fluide ou à une surcharge de sel, telle qu'une insuffisance cardiaque (en particulier, une insuffisance cardiaque congestive), une maladie rénale chronique, une maladie rénale en phase finale, une maladie hépatique et une rétention de fluide induite par un agoniste gamma du récepteur activé de la prolifération des peroxysomes (PPAR). La présente invention concerne également des composés et des procédés pour le traitement de l'hypertension. La présente invention concerne en outre des composés et des procédés pour le traitement de troubles du tractus digestif, comprenant le traitement ou la réduction de la douleur associée à des troubles du tractus digestif.
Applications Claiming Priority (5)
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US201762444335P | 2017-01-09 | 2017-01-09 | |
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US201762541097P | 2017-08-04 | 2017-08-04 | |
US62/541,097 | 2017-08-04 | ||
PCT/US2018/013020 WO2018129552A1 (fr) | 2017-01-09 | 2018-01-09 | Composés utiles pour le traitement de troubles du tractus digestif |
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CA3049678A1 true CA3049678A1 (fr) | 2018-07-12 |
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CA3049678A Pending CA3049678A1 (fr) | 2017-01-09 | 2018-01-09 | Composes utiles pour le traitement de troubles du tractus digestif |
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US (2) | US11242337B2 (fr) |
EP (1) | EP3565808A1 (fr) |
JP (2) | JP7292207B2 (fr) |
KR (1) | KR20190126775A (fr) |
CN (1) | CN110267944B (fr) |
AU (2) | AU2018205400B2 (fr) |
BR (1) | BR112019013956A2 (fr) |
CA (1) | CA3049678A1 (fr) |
IL (1) | IL267805B (fr) |
MA (1) | MA47207A (fr) |
MX (1) | MX2019008170A (fr) |
UA (1) | UA126283C2 (fr) |
WO (1) | WO2018129552A1 (fr) |
ZA (1) | ZA201904297B (fr) |
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US11242337B2 (en) * | 2017-01-09 | 2022-02-08 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
BR112019013963A2 (pt) * | 2017-01-09 | 2020-04-28 | Ardelyx Inc | inibidores de antiporte mediado por nhe |
WO2020051014A1 (fr) * | 2018-09-04 | 2020-03-12 | Teva Pharmaceuticals International Gmbh | Procédés pour la préparation de ténapanor et d'intermédiaires de ceux-ci |
GB201815018D0 (en) * | 2018-09-14 | 2018-10-31 | Univ Oxford Innovation Ltd | Enantiomeric compounds |
CN111954669B (zh) * | 2019-03-14 | 2023-04-07 | 深圳仁泰医药科技有限公司 | Nhe3抑制剂的晶型a及其制备方法和应用 |
CN113636960A (zh) * | 2021-08-24 | 2021-11-12 | 上海皓元医药股份有限公司 | 一种2-(氯磺酰基)环己烷-1-烯甲酸乙酯衍生物的制备方法 |
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US3926891A (en) | 1974-03-13 | 1975-12-16 | Dow Chemical Co | Method for making a crosslinkable aqueous solution which is useful to form soft, water-swellable polyacrylate articles |
US3997484A (en) | 1974-04-03 | 1976-12-14 | The United States Of America As Represented By The Secretary Of Agriculture | Highly-absorbent starch-containing polymeric compositions |
US3935099A (en) | 1974-04-03 | 1976-01-27 | The United States Of America As Represented By The Secretary Of Agriculture | Method of reducing water content of emulsions, suspensions, and dispersions with highly absorbent starch-containing polymeric compositions |
US4090013A (en) | 1975-03-07 | 1978-05-16 | National Starch And Chemical Corp. | Absorbent composition of matter |
JPS51125468A (en) | 1975-03-27 | 1976-11-01 | Sanyo Chem Ind Ltd | Method of preparing resins of high water absorbency |
JPS5346389A (en) | 1976-10-07 | 1978-04-25 | Kao Corp | Preparation of self-crosslinking polymer of acrylic alkali metal salt |
US4190562A (en) | 1977-04-04 | 1980-02-26 | The B. F. Goodrich Company | Improved water absorbent copolymers of copolymerizable carboxylic acids and acrylic or methacrylic esters |
US4470975A (en) | 1977-10-21 | 1984-09-11 | The Johns Hopkins University | Method and composition for the elimination of water from an animal body |
US4286082A (en) | 1979-04-06 | 1981-08-25 | Nippon Shokubai Kagaku Kogyo & Co., Ltd. | Absorbent resin composition and process for producing same |
JPS6025045B2 (ja) | 1980-03-19 | 1985-06-15 | 製鉄化学工業株式会社 | 塩水吸収能のすぐれたアクリル酸重合体の製造方法 |
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- 2018-01-09 KR KR1020197023352A patent/KR20190126775A/ko active IP Right Grant
- 2018-01-09 WO PCT/US2018/013020 patent/WO2018129552A1/fr unknown
- 2018-01-09 BR BR112019013956-7A patent/BR112019013956A2/pt active Search and Examination
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WO2018129552A1 (fr) | 2018-07-12 |
UA126283C2 (uk) | 2022-09-14 |
BR112019013956A2 (pt) | 2020-02-11 |
AU2022211830A9 (en) | 2022-09-08 |
JP2023052205A (ja) | 2023-04-11 |
AU2018205400A1 (en) | 2019-07-18 |
JP2020515516A (ja) | 2020-05-28 |
AU2022211830A1 (en) | 2022-09-01 |
US11242337B2 (en) | 2022-02-08 |
CN110267944A (zh) | 2019-09-20 |
IL267805B (en) | 2022-02-01 |
AU2018205400B2 (en) | 2022-07-14 |
MX2019008170A (es) | 2020-02-07 |
US20220306610A1 (en) | 2022-09-29 |
EP3565808A1 (fr) | 2019-11-13 |
ZA201904297B (en) | 2020-10-28 |
KR20190126775A (ko) | 2019-11-12 |
MA47207A (fr) | 2019-11-13 |
US20190359599A1 (en) | 2019-11-28 |
JP7292207B2 (ja) | 2023-06-16 |
IL267805A (en) | 2019-09-26 |
CN110267944B (zh) | 2024-03-08 |
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